Over the years I’ve seen many guys try their game on pretty girls. Some of these guys did well, but many did not so well. Most of us could stand to learn a thing or two about how to attract a woman like a gentleman. We’ll go over the do’s and dont’s of flirting. Guys, get a pen and paper, here come some grade A flirting tips.
But before we get into all of that, you need to realize one thing. Learning how to flirt with a beautiful woman isn’t about having a bag of tricks or a script. It isn’t about learning the art of seduction or manipulation, or anything else sleazy like that. This isn’t a David DeAngelo type of guide to flirting. Flirting like a Gentleman is about engaging a woman on an intellectual level, building a rapport with her, and chancing that at the end of the flirting she has become as interested in you as you are in her.
Making friends wasn’t terribly difficult in kindergarten, and if you treat this woman the same way your mother taught you to treat girls in kindergarten, you’ll do just fine. so RELAX, and realize that you’re you, she’s her, and that’s all that either of you needs to be.
Humor
Humor is a great way to engage a woman. You know the old saying, “a woman appreciates a man who can make her laugh.” When first meeting a woman though, it’s important to keep the humor clean and fun. It’s ok to tease, but make sure you aren’t offending anyone or teasing too much, as some girls are more sensitive than others.
Confidence vs. Arrogance
Women love a confident man. But most can’t stand an arrogant one. Whether you are a cheerfully confident guy or you’re just acting, make sure to steer clear of the arrogant kind of confidence. Remember, just because you feel good about yourself doesn’t mean you’re better than anyone else.
Compliment, Compliment, Compliment
I love compliments, you love compliments, and I’m pretty sure it’s safe to say that she will too. Compliments are a nice, pressure-free way to build rapport with a woman. Obviously the content of your compliment matters, though. “You have really pretty hair,” or “I love that jacket on you” are both good compliments, but “Your body is bangin in that dress” might not be. Use your better judgement on this one.
Hold a Gaze
It has been scientifically proven that women find a greater psychological attraction to men who can hold their gaze. Understand the difference between a gaze and a stare though, and don’t let things get weird. If she looks into your eyes, hold contact for just 1 second longer than you might feel comfortable doing. It’s a great way to get better at it. Pretty soon women that you have no intent on pursuing will find themselves wildly attracted to you. Well, maybe.
Chivalry
What would “A Gentleman’s Guide” be without chivalry. To some it’s dead, to others there is no relationship without it. As a gentleman you always remain chivalrous. This means you open doors for her, pull out her chair, offer your coat, and even walk arm in arm if she would like. You allow her up the stairs first (in case she falls, so you can save her) and you walk before her down the stairs, unless she insists, in which case you can walk together. If you asked her out, you pay for the entire night. If she asked you out, you offer to pay, but allow her the final decision. If she insists on paying, you allow her to and offer to take her out again (on your dime of course). A gentleman is not a gentleman without chivalry.
Excitement
Excitement is the driving force behind “the spark.” It can make or break her opinion of you. Some guys get away with being jerks and losers just because they are exciting as hell. You want to be that exciting guy. You want that girl to think you are straight out of an action movie, you’re so exciting. This doesn’t mean you have to ride a motorcycle and wear a leather jacket (although those wouldn’t hurt), but you should be enthusiastic about your interests. I once met a girl who was so enthusiastic about her knitting (that’s right, knitting, like a grandma) that I found it curiously attractive.
Also, you should show your excitement for the things that she’s into. You obviously don’t want to be jumping out of your chair with excitement, but you want her to know that you think her interests are cool.
Let Her Talk
We all love to talk about ourselves, and women are no exclusion. Once when out with a woman, I let her talk pretty much the entire night, and only said a few (very cool) things about myself. By the end of the night she was all talked out, but she had apparently had a great time, and found me to be very interesting. “How is that?” I asked. “I dunno, there’s just something about you that is intriguing.” she answered. You know what it was? It was that she felt good about our date because she talked about herself (the person she loves most) the whole time and didn’t find out much about me. I was a good listener, which she liked, and she didn’t know much about me, which made me mysterious. It’s a potent combination that women go crazy over.
Stay Positive
I learned a hard lesson once, and it’s not something that I’m ready to share. But let’s just say this: No matter how well things are going, one emotionally negative thing said could ruin everything. Dating is a fickle being, and it can swing from good to bad in .02 seconds flat. So as a general rule, keep your first dates positive, no matter what. Don’t talk about your dead grandmother, your dead-end job (unless it’s with humor), your lack of satisfaction in life, or anything else that might change the mood from something positive to something negative.
Keep The Mystery Alive
Ah the mystery again. It was so important that I decided to talk about it again. No matter how awesome you are, if a woman ends the night feeling like she knows everything about you, there is much less motivation for a second date. What’s new to find out? What exciting things could you possibly say? She’s heard all she needs to, and she’s moving on. So while it’s great to share things about yourself, keep the mystery alive, and keep a couple of great stories in the holster for other dates.
Be The Man
Let her wear the makeup and skirts, and you wear the pants and (insert manly thing here…). A woman may appreciate a sensitive guy, but not an overly sensitive one. Don’t hide your manliness, let it shine. Women like men, not boys, not metrosexuals, and not girls. They want a man to be a man. So do just that. Be the man she’s looking for.
Physical Contact
Used sparingly, physical contact can really create a bond between the two of you. A subtle touch of the wrist, knee, or even a pat on the arm or shoulder can really spark the fire. Don’t be the guy who is all over girls, nobody likes that dude. But when appropriate, practice the art of subtle communication through physical contact.
Create the Connection
Inside jokes, nicknames, and stories including the two of you… 3 things you should have in common with her by the end of the first few dates if you’re playing your cards right. A relationship of substance can be organically enhanced by simple things like creating inside jokes or building stories together. It gives her a sense that you two have a relationship already, even if you don’t.
Don’t Hide The Nerd Inside
Sure, you could hide the fact that you’re a level 78 Mage on World of Warcraft (I don’t actually know if there is a mage or whatever), but sooner or later she’s going to find all the action figures and magic cards. Plus, if it’s something you really like, why be ashamed? Is she really worth being someone else for?
Be yourself, as nerdy as you may be. If she’s the right fit, she’ll find it geeky endearing (I just made that up, but it works), or at the very least amusing. Oh and trust me, she has an inner nerd too. They always do.
Here are a few tiny tips to help you on your way
- Share a secret – builds rapport and helps solidify a connection
- Ask Questions - shows interest and allows you to learn about her
- Avoid talking about past relationships – nobody ever wants to hear this on a first date
- Give her all of your attention – don’t answer your phone, look at other girls, etc.
- Don’t flirt with others in front of her - self-explanatory
- Pay attention to language - Don’t curse if she doesn’t…
- Don’t talk about sex - it adds pressure. Save that talk for later.
So there you have it. The Gentleman’s Guide to Flirting. Of course no guide would be complete without a few other gentleman (and ladies) chiming in. So, let’s hear it. What would be your #1 tip for a gentleman in training? Leave your comments below and help a fella out!














Kudos on a great article! Entertaining and Informative!
Abe, I think you've hit one out of the park with this article. Good job! I would add this one:
BE HONEST. There is nothing worse to most woman than a man that lies to them. They will find you out, and when they do there will be hell to pay. Seriously I have seen SOOO many guys make this mistake. It doesn't even have to be a lie about something important. Here's the lady logic on that one. “If he lied to me about (insert white lie here) what ELSE is he lying to me about?” usually this is followed by, “How dumb does he think I am to think I wouldn't find out?” Now, all of that being said, you don't have to use a truth baseball bat when telling her that a dress doesn't look flatter her. Learning some tact and timing will go a long way! Remember if you are trying to build a relationship with this lady, you are in for the long haul! Don't pretend to be someone you aren't and don't hide what you really think. In the end it isn't fair to either of you.
Honesty, of course. I kind of hinted at it, with “Share a secret” and “Don't hide your inner nerd” but it deserves it's own mention. I never lie to women, because it's just easier to not have to play charades. Great tip!
I don't think that you can be honest at all… i little lie can help you to get fast to your goal!
I'm sure that may work for some, but it isn't the way a gentleman does things.
On the topic of chivalry, it's actually considered not very gentlemanly to have to woman walk up the stairs first since you would be able to look under her skirt.
Yes the skirt would have to be extremely short and these days women wear jeans/pants too, but still it's one of the rules like holding open a door and walking on the street-side of a sidewalk.